CAS 60142-96-3|gabapentin|Gabapentin|1-(Aminomethyl)-cyclohexaneacetic acid|2-[1-(aminomethyl)cyclohexyl]acetic acid|Neurontin|Gabapentine [INN-French]|Gabapentinum [INN-Latin]|Aclonium|Neurontin|Ga...

基本信息

化学结构

分子式

C₉H₁₇NO₂

分子量

171.23678

精确质量

171.12592879

电荷

InChI

InChI=1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12)

InChIKey

UGJMXCAKCUNAIE-UHFFFAOYSA-N

Canonic Smiles

NCC1(CCCCC1)CC(=O)O

Isomeric Smiles

OC(=O)CC1(CCCCC1)CN

计算属性

JChem

LogD (pH = 7.4)

-1.27

LogD (pH = 5.5)

-1.32

Log P

-1.27

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

4.63

极化表面积

63.32

极化性

18.92

摩尔折射率

46.33

LOG S

-1.13

数据来源

名称和标识

别名

Gabapentin1-(Aminomethyl)-cyclohexaneacetic acidNeurontinGabapentino [INN-Spanish]Gabapentino [Spanish]Gabapentinum [INN-Latin]Gabapentin GRGabapetinGabapentinGabapentine [INN-French]gabapentinFanatrexGabarone2-(1-(aminomethyl)cyclohexyl)acetic acid2-[1-(aminomethyl)cyclohexyl]acetic acid1-(Aminomethyl)cyclohexaneacetic Acid, Neurontin, GOE-3450Aclonium(1-Aminomethyl-cyclohexyl)-acetic acidgabapentin1-(Aminomethyl)cyclohexaneacetic acid

IUPAC传统名

gabapentin 2-[1-(aminomethyl)cyclohexyl]acetic acid

IUPAC标准名

2-[1-(aminomethyl)cyclohexyl]acetic acid

商标名

NeurontinNovo-GabapentinAclonium

API名称

Gabapentin

国际非专利药品(INN)

gabapentingabapentinagabapentinumgabapentine

名称和标识

数据登录号

化合物性质

药理学性质

相关基因信息

human ... ADORA1(134), CACNA2D1(781)rat ... Cacna1a(25398)

生物活性机理

GABA-like amino acid which penetrates the blood-brain barrier

regulator

Voltage-gated N-type calcium ion channels

化合物性质

分子相关蛋白质

分子图谱

暂无数据

点击上传数据

描述信息

DrugBank

DB00996

Drug Groups

approved; investigational

Description

Gabapentin (brand name Neurontin) is a medication originally developed for the treatment of epilepsy. Presently, gabapentin is widely used to relieve pain, especially neuropathic pain. Gabapentin is well tolerated in most patients, has a relatively mild side-effect profile, and passes through the body unmetabolized.

Indication

For the management of postherpetic neuralgia in adults and as adjunctive therapy in the treatment of partial seizures with and without secondary generalization in patients over 12 years of age with epilepsy.

Pharmacology

Gabapentin, an analog of GABA, is used as an anticonvulsant to treat partial seizures, amyotrophic lateral sclerosis (ALS), and painful neuropathies. Potential uses include monotherapy of refractory partial seizure disorders, and treatment of spasticity in multiple sclerosis, tremor. mood disorders, and attenuation of disruptive behaviors in dementia. Gabapentin has high lipid solubility, is not metabolized by the liver, has no protein binding, and doesn't possess the usual drug interactions.

Toxicity

Symptoms of overdose include ataxia, labored breathing, ptosis, sedation, hypoactivity, and excitation.

Affected Organisms

Humans and other mammals

Biotransformation

All pharmacological actions following gabapentin administration are due to the activity of the parent compound; gabapentin is not appreciably metabolized in humans.

Absorption

Rapid. Absorbed in part by the L-amino acid transport system, which is a carrier-mediated, saturable transport system; as the dose increases, bioavailability decreases. Bioavailability ranges from approximately 60% for a 900 mg dose per day to approximately 27% for a 4800 milligram dose per day. Food has a slight effect on the rate and extent of absorption of gabapentin (14% increase in AUC).

Half Life

5-7 hours

Protein Binding

Less than 3% of gabapentin circulates bound to plasma protein.

Elimination

Gabapentin is eliminated from the systemic circulation by renal excretion as unchanged drug.
Gabapentin is not appreciably metabolized in humans.

Distribution

* 58±6 L

Clearance

* 190 mL/min

References

• Mathew NT, Rapoport A, Saper J, Magnus L, Klapper J, Ramadan N, Stacey B, Tepper S: Efficacy of gabapentin in migraine prophylaxis. Headache. 2001 Feb;41(2):119-28. [Pubmed]

• Backonja MM, Serra J: Pharmacologic management part 1: better-studied neuropathic pain diseases. Pain Med. 2004 Mar;5 Suppl 1:S28-47. [Pubmed]

• Choudhuri I, Sarvananthan N, Gottlob I: Survey of management of acquired nystagmus in the United Kingdom. Eye. 2007 Sep;21(9):1194-7. Epub 2006 May 26. [Pubmed]

• Pande AC, Crockatt JG, Janney CA, Werth JL, Tsaroucha G: Gabapentin in bipolar disorder: a placebo-controlled trial of adjunctive therapy. Gabapentin Bipolar Disorder Study Group. Bipolar Disord. 2000 Sep;2(3 Pt 2):249-55. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Selleck Chemicals

S2133

Research Area: Neurological Disease
Biological Activity:
Gabapentin (Neurontin) is a pharmaceutical agent, specifically a GABA analogue. Gabapentin (Neurontin) was originally developed for the treatment of epilepsy, and currently, gabapentin is widely used to relieve pain, especially neuropathic pain. Its therapeutic action on neuropathic pain is thought to involve voltage-gated N-type calcium ion channels. It is thought to bind to the α2δ subunit (1 and 2) of the voltage-dependent calcium channel in the central nervous system. [1][2]

Sigma Aldrich

G154

Biochem/physiol Actions
Anticonvulsant with unknown mechanism of action; crosses the blood brain barrier; increases GABA concentrations in the brain and reduces excitatory amino acid neurotransmission, perhaps through its effects on voltage-gated calcium channels; exhibits antinociceptive, anxiolytic, neuroprotective and anti-epileptic effects.

TRC

G117250

Amino acid structurally related to γ-Aminobutyric Acid (GABA), designed to cross the blood brain barrier. Used as an anticonvulsant.

ChEBI

CHEBI:42797

A gamma-amino acid that is cyclohexane substituted at position 1 by aminomethyl and carboxymethyl groups. Used for treatment of neuropathic pain and restless legs syndrome.

描述信息

参考文献

PubChem文献

数据源提供

• Mathew NT, Rapoport A, Saper J, Magnus L, Klapper J, Ramadan N, Stacey B, Tepper S: Efficacy of gabapentin in migraine prophylaxis. Headache. 2001 Feb;41(2):119-28. Pubmed

• Choudhuri I, Sarvananthan N, Gottlob I: Survey of management of acquired nystagmus in the United Kingdom. Eye. 2007 Sep;21(9):1194-7. Epub 2006 May 26. Pubmed

• Backonja MM, Serra J: Pharmacologic management part 1: better-studied neuropathic pain diseases. Pain Med. 2004 Mar;5 Suppl 1:S28-47. Pubmed

• http://en.wikipedia.org/wiki/Gabapentin

• Vollmer, K.-O. et al.: Arzneimittel-Forshc., 36, 830 (1986)

• Saletu, B., et al.: Int. J. Clin. Pharmacol. Ther. Toxicol., 24, 362 (1986)

• Ger. Pat., 1976, Goedecke, 2 460 891; CA, 85, 94679h, (synth)

• Vollmer, K.O. et al., Arzneim.-Forsch., 1986, 36, 830, (metab)

• Bartoszyk, G.D. et al., Curr. Probl. Epilepsy, 1986, 4, 147, (rev, pharmacol)

• Pellock, J.M., Drugs of Today (Barcelona), 1998, 34, 31-35, (rev, pharmacol)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 346

• Goa, K.L. et al., Drugs, 1993, 46, 409, (rev)

• Griffiths, G. et al., Helv. Chim. Acta, 1991, 74, 309, (synth, bibl)

• Antiepileptic Drugs, 4th edn., (eds., Levy, R.H. et al), Raven Press, 1995

• Hengy, H. et al., J. Chromatogr., 1985, 341; 473, (hplc)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

IUPAC传统名

gabapentin 2-[1-(aminomethyl)cyclohexyl]acetic acid

IUPAC标准名

2-[1-(aminomethyl)cyclohexyl]acetic acid

商标名

NeurontinNovo-GabapentinAclonium

API名称

Gabapentin

国际非专利药品(INN)

gabapentingabapentinagabapentinumgabapentine

描述信息

DrugBank

DB00996

Drug Groups

approved; investigational

Description

Indication

Pharmacology

Toxicity

Symptoms of overdose include ataxia, labored breathing, ptosis, sedation, hypoactivity, and excitation.

Affected Organisms

Humans and other mammals

Biotransformation

All pharmacological actions following gabapentin administration are due to the activity of the parent compound; gabapentin is not appreciably metabolized in humans.

Absorption

Half Life

5-7 hours

Protein Binding

Less than 3% of gabapentin circulates bound to plasma protein.

Elimination

Gabapentin is eliminated from the systemic circulation by renal excretion as unchanged drug.
Gabapentin is not appreciably metabolized in humans.

Distribution

* 58±6 L

Clearance

* 190 mL/min

References

• Mathew NT, Rapoport A, Saper J, Magnus L, Klapper J, Ramadan N, Stacey B, Tepper S: Efficacy of gabapentin in migraine prophylaxis. Headache. 2001 Feb;41(2):119-28. [Pubmed]

• Backonja MM, Serra J: Pharmacologic management part 1: better-studied neuropathic pain diseases. Pain Med. 2004 Mar;5 Suppl 1:S28-47. [Pubmed]

• Choudhuri I, Sarvananthan N, Gottlob I: Survey of management of acquired nystagmus in the United Kingdom. Eye. 2007 Sep;21(9):1194-7. Epub 2006 May 26. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Selleck Chemicals

S2133

Sigma Aldrich

G154

TRC

G117250

Amino acid structurally related to γ-Aminobutyric Acid (GABA), designed to cross the blood brain barrier. Used as an anticonvulsant.

ChEBI

CHEBI:42797

A gamma-amino acid that is cyclohexane substituted at position 1 by aminomethyl and carboxymethyl groups. Used for treatment of neuropathic pain and restless legs syndrome.

参考文献

PubChem文献

数据源提供

• Mathew NT, Rapoport A, Saper J, Magnus L, Klapper J, Ramadan N, Stacey B, Tepper S: Efficacy of gabapentin in migraine prophylaxis. Headache. 2001 Feb;41(2):119-28. Pubmed

• Choudhuri I, Sarvananthan N, Gottlob I: Survey of management of acquired nystagmus in the United Kingdom. Eye. 2007 Sep;21(9):1194-7. Epub 2006 May 26. Pubmed

• Backonja MM, Serra J: Pharmacologic management part 1: better-studied neuropathic pain diseases. Pain Med. 2004 Mar;5 Suppl 1:S28-47. Pubmed

• http://en.wikipedia.org/wiki/Gabapentin

• Vollmer, K.-O. et al.: Arzneimittel-Forshc., 36, 830 (1986)

• Saletu, B., et al.: Int. J. Clin. Pharmacol. Ther. Toxicol., 24, 362 (1986)

• Ger. Pat., 1976, Goedecke, 2 460 891; CA, 85, 94679h, (synth)

• Vollmer, K.O. et al., Arzneim.-Forsch., 1986, 36, 830, (metab)

• Bartoszyk, G.D. et al., Curr. Probl. Epilepsy, 1986, 4, 147, (rev, pharmacol)

• Pellock, J.M., Drugs of Today (Barcelona), 1998, 34, 31-35, (rev, pharmacol)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 346

• Goa, K.L. et al., Drugs, 1993, 46, 409, (rev)

• Griffiths, G. et al., Helv. Chim. Acta, 1991, 74, 309, (synth, bibl)

• Antiepileptic Drugs, 4th edn., (eds., Levy, R.H. et al), Raven Press, 1995

• Hengy, H. et al., J. Chromatogr., 1985, 341; 473, (hplc)

生物活性

PubChem BioAssay

化合物性质

药理学性质

化合物信息

ID:869